Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H9N3 |
| Molecular Weight | 111.1451 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCC1=CNC=N1
InChI
InChIKey=NTYJJOPFIAHURM-UHFFFAOYSA-N
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
Histamine is a depressor amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and a centrally acting neurotransmitter. Phosphate salt of jistamine was used as a diagnostic aid for evaluation of gastric acid secretory function. In addition, this compound is used as a positive control in evaluation of allergenic (immediate hypersensitivity or "Type I") skin testing. In addition, histamine is being studied for treatment of multiple sclerosis. It was approved, that histamine physiological functions are mediated by four 7-transmembrane G protein-coupled receptors (H1R, H2R, H3R, H4R) that are all targets of pharmacological intervention. The receptors display molecular heterogeneity and constitutive activity. H1R antagonists are long known antiallergic and sedating drugs, whereas the H2R led to the development of H2R-antagonists that revolutionized stomach ulcer treatment. The H3R is an auto receptor and heteroreceptor providing negative feedback on histaminergic and inhibition on other neurons. The H4R occurs on immuncompetent cells and the development of anti-inflammatory drugs is anticipated.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 |
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Target ID: CHEMBL1941 |
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Target ID: CHEMBL264 |
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Target ID: CHEMBL3759 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | HISTAMINE PHOSPHATE Approved UseIndications and Usage Uses temporarily relieves symptoms due to sinus discomforts associated with inflamed sinuses, hay fever or upper respiratory allergies: sinus pain and pressure runny nose sinus headaches sore throat nasal congestion dry mucus membranes sneezing itchy, burning eyes Reference image sinus.jpg Launch Date1939 |
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| Primary | Unknown Approved UseUnknown |
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| Diagnostic | HISTAMINE PHOSPHATE Approved UseHistamine phosphate is indicated as a diagnostic aid for evaluation of gastric acid secretory function. Anacidity (achlorhydria) in response to histamine may indicate pernicious anemia, atrophic gastritis, adenomatous polyps of stomach, or gastric carcinoma. Gastric hypersecretion in response to histamine may indicate duodenal ulcer or the Zollinger-Ellison syndrome. Launch Date1939 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12092744 |
1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
HISTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1877 nM × min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12092744 |
1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
HISTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12092744 |
1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
HISTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Pharmacological studies of antipsychotic drug, penfluridol. 2. General pharmacological properties]. | 1976 Jul |
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| Diesel exhaust particulates upregulate histamine receptor mRNA and increase histamine-induced IL-8 and GM-CSF production in nasal epithelial cells and endothelial cells. | 1999 Jan |
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| Selective substrates for non-neuronal monoamine transporters. | 1999 Jul |
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| H2 histamine receptor-mediated increase in intracellular Ca2+ in cultured human keratinocytes. | 1999 Sep |
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| Identification of a histamine H(3)-like receptor in the zebrafish (Danio rerio) brain. | 2000 Aug |
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| Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles. | 2000 Jun |
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| Molecular cloning and characterization of a novel type of histamine receptor preferentially expressed in leukocytes. | 2000 Nov 24 |
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| Histamine H(3) receptors depress synaptic transmission in the corticostriatal pathway. | 2001 |
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| Predictive markers of asthma exacerbation during stepwise dose reduction of inhaled corticosteroids. | 2001 Feb |
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| Inhibitory action of water soluble fraction of Terminalia chebula on systemic and local anaphylaxis. | 2001 Feb |
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| A human tissue-engineered vascular media: a new model for pharmacological studies of contractile responses. | 2001 Feb |
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| Altered processing of fibronectin in mice lacking heparin. a role for heparin-dependent mast cell chymase in fibronectin degradation. | 2001 Feb 9 |
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| Comparison of montelukast and fexofenadine for chronic idiopathic urticaria. | 2001 Jan |
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| Preclinical profile of the monodisperse iodinated macromolecular blood pool agent P743. | 2001 Jan |
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| Urticaria induced by cetirizine. | 2001 Jan |
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| Interleukin-4-positive mast cells are highly associated with the extent of immediate allergic wheal reaction in the skin. | 2001 Jan |
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| A randomized, double-blind, crossover comparison among cetirizine, levocetirizine, and ucb 28557 on histamine-induced cutaneous responses in healthy adult volunteers. | 2001 Jan |
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| Effect of cetirizine on bronchial hyperresponsiveness in patients with seasonal allergic rhinitis and asthma. | 2001 Jan |
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| Inhibition by glucocorticoids of the mast cell-dependent weal and flare response in human skin in vivo. | 2001 Jan |
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| Effect of the long-acting tachykinin NK(1) receptor antagonist MEN 11467 on tracheal mucus secretion in allergic ferrets. | 2001 Jan |
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| Antihistamines. | 2001 Jan |
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| Medical therapy for gastroesophageal reflux disease. | 2001 Jan |
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| Regulatory effect of histamine H1 receptor antagonist on the expression of messenger RNA encoding CC chemokines in the human nasal mucosa. | 2001 Jan |
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| Premedication with antihistamines may enhance efficacy of specific-allergen immunotherapy. | 2001 Jan |
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| Dysregulation of the IgE/Fc epsilon RI network in HIV-1 infection. | 2001 Jan |
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| Expression and biological significance of Ca2+-activated ion channels in human keratinocytes. | 2001 Jan |
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| Intraluminal acid and gastric mucosal integrity: the importance of blood-borne bicarbonate. | 2001 Jan |
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| The rat H3 receptor: gene organization and multiple isoforms. | 2001 Jan 12 |
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| Luminal Nalpha-methyl histamine stimulates gastric acid secretion in duodenal ulcer patients via releasing gastrin. | 2001 Jan 26 |
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| Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
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| Interactions of inflammatory mediators stimulating release of calcitonin gene-related peptide, substance P and prostaglandin E(2) from isolated rat skin. | 2001 Mar |
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| Correlation between neutral endopetidase (NEP) 3.4.24.11 in serum and the degree of the bronchial hyperreactivity. | 2001 Mar 2 |
Sample Use Guides
The skin in the test area should be cleansed with alcohol and air dried.
The histamine control skin test solution should be placed at the same site with the other skin test antigens, either on the patient's back or on the volar surface of the forearm. The patient should be placed in a comfortable position before the testing is begun.
For the prick test, a sharp needle is used to puncture the skin, but not to draw blood. If the scratch test is used, carefully break or scratch the skin with a sterile scarifier. Do not draw blood. Each scratch should be about 2 mm - 4 mm in length.
A small drop of the histamine base 1 mg/mL (Histamine Phosphate 2.75 mg/mL) is placed on the abraded skin site no closer than 4 or 5 cm from an adjacent test site. Some physicians prefer to place the solution on the test area and then prick through the drop with a sharp needle.
Route of Administration:
Parenteral
Histamine prevented monocytic apoptosis induced by serum deprivation, CD95/Fas ligation, or dexamethasone in a dose- and time-dependent fashion. The inhibitory effects of histamine on monocytic apoptosis were blocked by an H2R antagonist, and mimicked by an H2R agonist. Histamine also up-regulated the expression of Bcl-2 and Mcl-1, and inhibited the activation of caspase-3. The culture supernatants from histamine-treated monocytes inhibited monocytic apoptosis, which was partly reversed by the removal of IL-10. Monocytes cultured with anti-IL-10 mAb and histamine did not exhibit an inhibitory effect on apoptosis. The histamine-induced anti-apoptotic effect was attenuated when monocytes were cultured in the presence of a cAMP inhibitor.
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34316-0
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C687
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127199
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2416-6
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C2139
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35260-9
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43577-6
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44371-3
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C73238
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51-45-6
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HISTAMINE
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SUB14107MIG
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ACTIVE MOIETY
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